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Name: Doesn't Hurt to Ask
Rating: 4.3 (656 reviews)
Author: Trey Gowdy

Trey Gowdy

Using the Power of Questions to Communicate, Connect, and Persuade

4.3 (656 ratings)

22 mins

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Doesn't Hurt to Ask
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What’s in it for me? Learn how to advocate for your beliefs by asking questions.

When you’re trying to convince someone of something, you likely often take the route of stating the facts, arguments, and opinions that corroborate your belief. But the author knows a better way. In his work as a prosecutor, and later as a congressman, he discovered a much more powerful tool of persuasion: asking questions.

Asking the right questions doesn’t just work in court or Congress. It’s a skill that can serve all of us, whether it be in the boardroom, at school, or during a family Thanksgiving dinner. By learning how to nudge others in your direction, you can increase your argumentative power in almost every area of your private and professional life.

Whether you’re trying to convince someone to give you a job, a loan, or a second chance, these blinks will teach you how to harness the power of questions.

In these blinks, you’ll learn

why a stupid question is better than a stupid answer;
how you can turn any silly argument into a passionate speech on freedom and justice; and
why you should occasionally “flog a dead horse.”

Persuasion is a subtle art, and questions are its greatest tools.

Are you ready to start winning every argument you ever have? Are you ready to grind your opponents into the ground with your debating skills?

Then these blinks are not for you.

Persuasion isn’t about annihilating your opponents. It’s about listening to them, communicating with them, and advocating for your own beliefs in a compelling way. Think about it: how many times have you changed your mind because someone kept bombarding you with their opinions?

Questions work so well because they put the focus on your conversation partner, and nudge them in the right direction without making them react defensively. The author knows about this firsthand. He only got into law after a friend’s mom asked him a bunch of really great questions.

The key message here is: Persuasion is a subtle art, and questions are its greatest tools.

The author had always planned to work construction jobs with a friend when he’d finished high school. One day though, his friend’s mom picked up on the topic. She asked him, “What are you going to do next, honey?” After he answered, she asked a follow-up question. And then another one. And another one. By the end of the interview, he had decided that he wanted to become a lawyer.

His friend’s mother didn’t make a single evaluative statement to persuade him – she simply let him persuade himself. That’s the power of asking questions.

Now, let’s make one thing clear before you get started: there is such a thing as a stupid question. One time during a robbery trial, the author’s witness reported that the suspect “had a blue bag in his hand.” The author immediately fired off a follow-up question: “Okay, what color was the blue bag?” The laughter that ensued in the courtroom should be proof enough that stupid questions do exist.

Still, any stupid question is better than a stupid assertion. Imagine someone asking you, “Who wrote Hamlet?” That question reveals a pretty big knowledge gap. But now imagine someone telling you, “George Washington wrote Hamlet.” That’s not just a knowledge gap; that’s a knowledge gap the person isn’t even aware of. Who would you trust more in an honest debate – a person who is uninformed, or a person who is misinformed?

Know your objective, your facts, and your jury.

In a court case, the prosecutor needs to convince the jury to almost 100 percent. If there’s even a little bit of doubt about the defendant’s guilt, there likely won’t be a conviction.

In real life, though, it’s nearly impossible to convince someone beyond a doubt – and that’s especially true when it comes to topics like politics, business strategy, or family values, which almost always involve opinions and value judgments.

Different types of questions work in different situations.

The author once found himself in a live TV interview with President Trump on the topic of fairness in politics. He could have started by simply stating his opinion on the issue at hand. But instead he asked, “Why is our justice system more respected than our political system?”

Without stating his opinion outright, the author still made a comparison between the two systems. And he set up the president on a path to discussing why that is – even though the author had his own opinion on that, too. The author had chosen the right question, at the right time.

To be convincing, be sincere.

The author was once told that the secret to being a successful litigator is learning to fake sincerity.

Now, that’s a bit of a paradox. You can’t really fake being sincere. But you can draw on real emotions that will make you seem more genuine, credible, and likable to your audience.

Impeach an argument by questioning someone’s facts, logic, or character.

You’ve just learned about the three main killers of sincerity and credibility: insults, hypocrisy, and lying. If you’re not careful, they can easily destroy your argument. But if you know how to use credibility killers against your opponent, they can work wonders for you.

Credibility killers, in a word, can help you impeach. Now, you might only have heard the term impeachment when referring to a president. But here the word has a different meaning.

Fine-tune your persuasion skills by measuring, repeating, and repackaging.

“Do you agree America is more respected worldwide now than under President Obama?” A friend once asked the author this during a round of golf.

Instead of answering the question, the author asked his friend to define his terms. He asked, What does “worldwide” mean in this case? What does “more respected” mean? And where is the cut-off for either? His friend didn’t have an answer.

If your argument is failing, divert, deconstruct, double-down, or play the victim.

Even if you’re a master of persuasion, you can’t always nail it. Sometimes, you’ll just have to cut your losses and walk away. But there are a few strategies that can help you mitigate the damage of a failed argument.

The best cure, as always, is prevention. You can avoid backing yourself into a corner by having a good sense of your weaknesses. When preparing your argument, you might be tempted to linger on the bits and pieces that work particularly well. But you should spend just as much time preparing and padding your weakest points – instead of simply hoping that they won’t come up.

To master the art of persuasion, set the right expectations and stay open.

As a district attorney, the author recruited many young litigators. But before he hired anyone, he would make them prove their persuasion skills with a simple task: they had five minutes to convince him to go see their favorite movie.

Sounds easy enough, right? Still, even these young law professionals often did very poorly. The good news, though, is that they got better at persuasion over time as they practiced on real-life cases in court.

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What is Doesn't Hurt to Ask about?

Doesn’t Hurt to Ask (2020) teaches the subtle art of persuasion through one unconventional tool: asking questions. Former congressman Trey Gowdy explains how thoughtful questions can help you reach your audience, communicate your message, and win people over – whether that’s in a courtroom, a business meeting, or at the dinner table.

Best quote from Doesn't Hurt to Ask

The art of persuasion is not about winning people over but bringing people closer together.

—Trey Gowdy

Who should read Doesn't Hurt to Ask?

Exhausted parents looking to win their kids over in arguments
Politically engaged people who want to advocate for their beliefs more effectively
Anyone looking to improve their negotiation skills in their private or professional lives

About the Author

Trey Gowdy is a former federal prosecutor and district attorney from South Carolina. In 2010, he was elected to Congress, where he chaired the House Committee on Oversight and Government Reform and the Select Committee on Benghazi. With his friend Tim Scott, he co-authored the New York Times best seller Unified – How Our Unlikely Friendship Gives Us Hope for a Divided Country.

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